In each instance, the target of Trump’s petty ire was a black sports figure publicly rejecting his Make America Great Again siren song at a time when members of marginalized groups are speaking up about the existential threat posed by a president appealing to the surging tide of white supremacy. It is quite the trick for a president to publicly belittle African Americans while ignoring freshly ravaged Latino Americans in blacked-out Puerto Rico, but Trump somehow makes it seem as natural as jumping on Twitter to respond to whatever mess Fox News just reported.

But Trump is an equal opportunity grudge-holder and score-settler, whose call to fans to boycott the NFL is a direct shot at the wealthy white businessmen—many of whom supported his campaign—who rejected him from their club.

It was less than three years ago that Trump tried and failed to buy a NFL franchise. “The @nfl games are so boring now that actually, I’m glad I didn’t get the [Buffalo] Bills. Boring games, too many flags, too soft,” is how the Donald summed up his failure, which was really just a matter of Buffalo Sabres owner Paul Pegula outbidding him by a reported $400,000. “Football has become soft like our country has become soft,” said Trump on the 2016 campaign trail, clearly showing none of the classic behavioral traits of a rejected paramour.

Trump’s salty broadsides on the NFL, however, are more than just the reflexive stumping of a man who never met a failure he couldn’t recast into a confirmation of his own self-proclaimed superiority. About 34 years before he tried to buy into the league, Trump tried to go head-to-head with it. That play went about as well as his bankrupted casinos, or his presidency so far.

The inaugural 1983 season of the United States Football League made clear the enormous challenge the upstart league had taken on. Despite solid ratings on ESPN and ABC and a league-wide average attendance of 25,000 per game, the league took on six new owners after its first season in order to offset losses via franchise fees. That was its first mistake. The second was allowing Donald Trump to purchase the New Jersey Generals franchise from Oklahoma oil magnate J. Walter Duncan.

“If God had wanted football in the spring he wouldn’t have created baseball,” said Trump soon after joining the minor league owners’ club. You see, even though Trump had bought an ownership stake in a spring football league, he considered the idea of spring-time football an unacceptable nod in the direction of the NFL’s primacy. All through Trump’s first season, he aggressively lobbied his fellow owners to switch to a fall schedule and challenge the NFL on its own terms despite the fact that the USFL’s on-field product was little more than a second-rate NFL. The idea, for Trump at least, was that the USFL could force a merger and the owners of the more valuable franchises would Trojan horse their way into the NFL owners’ club.

By preying on the league’s more weak-willed and less financially solvent owners, Trump eventually got the fight he so publicly thirsted after. The league switched to a fall schedule in 1986 even as it fell apart under the burden of its debts and mismanagement. Attendance and ratings quickly hit the basement. ABC withheld rights fees and ESPN demanded a contract renegotiation after the league violated its deals with both by moving franchises to smaller media markets in order to avoid direct competition with the NFL and pave the way for the hoped-for merger that would never even come close to fruition.

With the walls of his own hubris closing in on him, Trump resorted to anti-monopoly litigation against the NFL. He hired Harvey D. Myerson, a lawyer with little in the way of antitrust litigation experience but who mirrored Trump’s own boisterous persona, to lead the case. A jury ruled that the NFL did engage in monopolistic practices against the USFL and ruled in favor of the plaintiffs. Damages, after standard antitrust trebling and interest, totaled $3.76. Even Trump’s victory came with a public indignity that made him out to be just a bum in the eyes of the public. LeBron James surely agrees.

The USFL ceased operations in 1987. This came after the league’s owners turned down a combined $245 million in rights deals totalling $67 million annually from ESPN and ABC to pursue its quixotic litigation against the NFL. Donald Trump never even got his wish of going head-to-head with the NFL on Sundays as the league’s financial collapse was so rapid that it couldn’t afford to put on games for the planned fall schedule of 1986. It remains the most thorough and public failure of Donald Trump’s life and it’s quite obvious that he hasn’t forgotten a second of that years-long testament to the hopelessness of tilting at windmills.

In the same years that Trump—who boasted about shaking down New York Giants great Lawrence Taylor for nearly a million dollars in 1984 even as he told the IRS he’d made no income at all that year—was bringing down his fellow USFL owners in his failed bid to bring down the NFL, he was regularly palling around with black athletes and entertainers.

“People ask me, ‘Is he a racist?’” said Al Sharpton, who knew Trump socially when the then-real estate developer was often seen with heavyweight boxers and entertainers he needed to fight and play in his Atlantic City venues before those went bust. “It’s worse than that. He’ll use racism if it suits his purpose.”

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“His obsession as far as I could tell is that he wanted to beat [Las Vegas hotel and casino magnate] Steve Wynn and have the big events in A.C. like they had in Vegas. And he couldn’t do that without black entertainers, but now all of a sudden those same guys are villains and pariahs. They’re whatever’s useful to him,” Sharpton, who ran for the Democratic presidential nomination himself in 2004, told The Daily Beast in a phone interview on Monday.

“It’s no accident he’s in Huntsville, Alabama calling black mothers ‘bitches.’ Here’s a guy who stood by Mike Tyson” when the heavyweight was accused and then convicted of rape “calling fine, upstanding athletes sons of bitches because they are protesting police brutality and racial inequities.”

“He was never a very personable guy, but he’d come to the events and sit there and act like he was enjoying it. He was always a kind of guy, like Don King, who wanted to dominate the room, so it wasn’t like you’d sit and talk with him about life but he’d certainly socialize,” said Sharpton, who recalled that “when Mike Tyson bought a house in Connecticut and had a housewarming, I went and Trump was there but it was business. You’d meet guys like that all the time, who’d be there because they wanted to book the artists. It was business.”

It still is, says Sharpton. “I don’t think he believed it when when he was being friendly to all of us and I don’t think he believes now. I think he’ll do whatever works for him, and that makes it more dangerous.”

And so here we are, with a president calling for boycotts of the NFL while mostly ignoring the fact that athletes in every major sport are lining up to take public pot-shots at him.

While Trump will gladly play to the darkside of identity politics, it’s obvious that he’s also using his presidency to settle a decades-old grudge with the NFL. Let that wash over you: The most powerful man in the world is using his office to get even with a sports league by… being mean to its players and owners on Twitter?

The sad part is that it all makes a sick sort of sense. Donald Trump, a man bred to carry family grudges of every sort across time and space, has dedicated his life to sticking his name on gaudy monuments to self-promotion lest he ever consider his innumerable list of personal and professional failures.

After decades of failing up, Donald Trump wants for nothing, yet still feels he is due a certain status and acclaim, and is angered when those are questioned. That doesn’t make him a white supremacist, per se, but it is the shorthand demand of every garden-variety white supremacist: The correction of a social order that they believe has ceased to sufficiently favor them at the expense of others. It is an ideology based on a grudge against the other — other Americans! — that can only be settled through a radical restructuring of society to make things great again.

“I think his lounge act resonated because a lot of people who feel disconnected and left out misunderstood the chip on his shoulder, which is there because the real elites never accepted him,” said Sharpton. “He’s not one of the people left out—he just shares a common enemy with them, and I think he played to that but his policies are going to hurt the people who supported his act as much as they’re going to hurt us.”

This isn’t four-dimensional chess. Power is nothing more than a means of displaying power to Trump, and he is now the most powerful human on the face of the Earth.

The game is over for him. All that he has left is lording his victory over everyone who has or ever will dare question his primacy. That’s why he’s just as comfortable calling for a black female sports anchor to be fired as he is calling for the boycott of a league ruled by white men who rejected his bid to join their club. Both are just grudges to be settled and nothing more.